8 Marriage Proposal Tips I Should Have Known

About a week ago I wrote about the intricacies involved buying an engagement ring for your wife-to-be, but let me tell you, the actual act of proposing definitely isn’t any easier. It’s the make or break moment that anything and everything that you as a couple have gone through before leads to. The time when you first met and awkwardly introduced yourself and made jokes that even you didn’t think were funny. The time you asked her on a first date to the movies and were too scared to put your arm around her. The time you dropped her off home and finally had the courage to give her a first kiss. The time of your first disagreement when she refused to talk to you because you left the toilet seat up or didn’t make the bed. None of that matters anymore, because all of it comes down to this very moment when you get down on one knee and ask her that age old question. There is no beating around the bush anymore. The question is direct and clear as can be: “Will you marry me?”

The answer that she will give you is the only thing that matters; it’s either a yes, or a no. At that moment you will know whether you’ll be spending the rest of your life with the woman you have been with for all this time, or whether you will be living alone again in a house of dirty toilet seats and unmade beds. All that emotion that you have had to bottle up for so long as you planned the proposal is released in one go, and a wave of relief and happiness finally sets over you when know that the answer is yes. That’s if all goes well, and the answer is yes of course. There is always a possibility of a no (no matter how many signs she showed she wanted to marry you) which makes the whole process that much more nerve-wrecking when you do get down on your one knee.

Thankfully, I did eventually receive a yes, but that’s about the only thing that went right that evening. My proposal was far from perfect. I didn’t plan anything too elaborate, and having heard of proposals while skydiving or in flying space, my simple idea of surprising her in a restaurant seemed like a very basic one on all accounts. It was one for very little scope of error, but didn’t quite turn out that way.

That’s why, for regular guys like you and me, I have out of the kindness of my heart, put together a list of marriage proposal tips on what to do when planning to propose to your girlfriend. Sure, screwing up your proposal creates some great laughter at the time, but is that really how you want it to be remembered for the rest of your life? Is that the story you want to hear your wife tell your children when they ask how daddy proposed to mommy? If the answer is yes, please stop reading here.

#1 Make Sure You Speak Her Parents Language Fluently or Bring a Translator

So long story short, I had planned the proposal for quite some time at this stage, and thought it would be polite to ask her parents for permission. Given that I travel to Jakarta, Indonesia (where Diana’s parents live) quite frequently for work, I figured it wouldn’t be long before I’d have the opportunity to meet them. And surely, about two weeks prior to when I had planned the proposal, I had to go to Jakarta for business and took it on myself to meet her parents to ask them for their daughter’s hand in marriage. The trick was that I had to do it all in Indonesian given that her parents speak very little English.

I had picked up some basic Indonesian over the last year or so from having gone there on a number of occasions, so I was able to complete simple tasks like asking for directions, going to the supermarket, or asking where the restroom was. Confessing my undying love for their daughter and wanting to spend the rest of my life with her, however, was another matter altogether. As it turned out, it was something that my limited Indonesian vocabulary wasn’t quite able to justice to. What was meant to be a convincing speech professing my unfaltering love for their daughter while asking for their permission on her hand in marriage, eventually (after much stuttering) turned into “Aku mau menikah Diana, bisa ga?”, or “I want to marry Diana, can or not?”. Not quite what her parents had in mind when imagining the day that a man would ask for her daughter’s hand in marriage and confess his love, but I’m sure it wasn’t quite like this. Nonetheless, the answer was yes, or at least that’s what I understood from what they said. They didn’t stop me when I proposed to her so that must have been the answer…

That’s why, my friends, if you decide to marry a girl whose parents’ language you don’t speak fluently, keep learning before you ask them, or bring someone that you can trust and translate for you. It will allow you to do justice your request, and you’ll actually be able to understand the subsequent answer.

#2 Do Your Research Up Front to Minimize Unforeseen Variables

Please make sure you do your research up front to ensure that there won’t be any unforeseen variables that may throw a spanner in the works for your proposal plan. Unfortunately, this wasn’t one of the marriage proposal tips I had taken into account when I started planning.

The week prior to the proposal, Diana was in Indonesia for work and was staying with her parents in Jakarta for the week. I was on a business trip in Vietnam that same week, and was planning to secretly fly in from Ho Chi Minh City, connecting through Singapore, on the evening Friday of that week to surprise her. Her parents would take her out for dinner to a restaurant, and my plan was to walk into the restaurant unannounced, and get onto my one knee and propose while catching her off-guard. I had visualized it all before. Everyone would start crying as soon as I got onto my knee, customers in the restaurant would start cheering, she would say yes, we would hug and kiss, and we would live happily ever after. Unfortunately, this wasn’t quite how it happened.

My plane landed at around 6.30PM in the evening, and the plan was to meet them for dinner at around 7.30PM. Unfortunately, for any of you that know Jakarta, it possibly has the worst traffic in the world, particularly on Friday evenings. It turned out that the expectation of being there at 7.30PM was completely unreasonable. Instead of being at the restaurant at that time, I was spending it with a somewhat odorous, albeit friendly, taxi driver. Not quite what I had in mind.

Please, my friends… take any variables that you can into account, and do your research up front. For example, if you’re driving somewhere, make sure you take into account the traffic. You don’t want to be spending the moment you should be proposing to your future wife with a taxi driver.

In order to be able to surprise Diana, I had to tell her a white lie. She had been asking me if I could join her in Jakarta the weekend I had planned my proposal. She suggested that we spend some time with her parents. Little did she know what I had in store for her, or so I thought.

I had to make it seem like I couldn’t make it to Jakarta in order to keep the surprise. I told her that I would try to make the earlier flight from Ho Chi Minh City to Singapore so that I could catch the connecting flight Jakarta if my work meeting ended up finishing early, but that it would be very unlikely. I knew, of course, that I would be telling her last-minute on Friday evening that the meeting had run late and I wouldn’t be able to make the flight to Jakarta and would have to go back to Singapore instead. I called her, and it all went to plan… that is until we said goodbye as we hung up the phone.

I have no idea where it came from, but just as we were about to hang up the phone, I said “See you soon” to which she responded “See you soon?!” It just slipped out, I have no idea how it happened. I tried to talk my way out of it by saying, “Oh yeah, I mean a couple of weeks from now” and thought I did a pretty good job to recover from my obvious blunder, but as I found out later, this had seriously raised her suspicions and she knew something was up. There is no fooling a woman, is there?

One of the marriage proposal tips here is that you have to be extremely good at making up a credible white lie, but most importantly making sure that you are capable of sticking to it. If not, you can say your surprise proposal goodbye! Women have a 6th sense for this kind of stuff, and can pick up any inconsistencies in your story from a mile away. Make sure your story is watertight!

#4 Make Sure Her Parents Can Keep a Secret

Equally important to being able to keep a secret yourself, is for her parents (or anyone else that you tell in advance for that matter) to be able to keep a secret, and keep it in confidence. When I say keeping a secret, I don’t just mean not telling anyone else, I also mean not engaging in activities that may raise suspicion. Even though Diana’s didn’t tell her outright, they weren’t particularly skilled at not raising any suspicions.

Firstly, I had asked Diana’s father to book a restaurant for the Friday evening of the proposal and to take her for dinner. It is quite usual for her family to go out for dinner, so I figured this wouldn’t set off any alarm bells. And it didn’t. However, when her father asked her to make sure that she made it on time to the restaurant, because there was an “important event” scheduled without providing any additional details, it was a different matter altogether. This followed a barrage of questions from Diana. An important event? What do you mean? What kind of event? Diana’s father had dug himself a hole that was impossible to climb out of, and even though Diana didn’t know exactly what was planned, she knew something was up.

To make matters worse, earlier in the week when Diana was at home, she caught her father in another act that raised her suspicions. Her father was testing out the air-conditioner in the guest bedroom. This is a room that is never ever used… except for when I visit. It didn’t take long to figure out that two and two is four. I really appreciate her father’s concern around my sleeping conditions, but maybe he could have checked while she wasn’t right there?! You’ll be glad to know that the air-condition unit was in fine working order though! Lucky me!

#5 Turn Off Your Phone When You Are Meant to Be in an Airplane

As I sat in the taxi on the way to the restaurant, with my new taxi driver buddy, at around 8 PM, the time when I had told Diana I would be high up in the sky flying back from Ho Chi Minh City to Singapore my phone suddenly started ringing. It was Diana. I panicked and decided to let the phone ring and not pick up, but I knew the fact that it was ringing would be enough give away that I wasn’t in an airplane. Or maybe I somehow magically picked up a signal while flying at 45,000 feet in the air? Not really believable.

Unfortunately, it wasn’t long before the phone started ringing again. Diana can be very stubborn and persistent at times. At this point I must admit that I started to worry a little. Why is she calling me twice in a row? Did something happen? I eventually gave into the urge to pick up the phone after which I nonchalantly heard her voice asking me “Where are you, and what time are you getting here?” Apparently her mother had been equally worried about the fact that I hadn’t arrived at the restaurant yet, and was concerned. She was so concerned that she had told Diana that I was in Jakarta on the way to meet them but was afraid something may have happened. I was fine.

That was the end of the first surprise of me arriving unannounced at the restaurant. She knew I was on the way, but at least she didn’t know that I was planning to propose to her.

#6 Wear Baggy Clothes to Hide the Box for the Ring

I did finally make it to the restaurant at around 10.00PM (over two hours late) after spending three hours with Mr. Taxi Man. As I walked in, they had already finished dinner. I had to make do with the leftovers. This hardly seemed like the ideal setting to propose, and I couldn’t get myself to do it in the restaurant. Most tables were deserted, and the staff had already started to clean up the restaurant in advance of the next day. My dreams of having the family cry as I got onto my one knee, with spectators cheering in jubilation from the sidelines, all shattered into tiny little pieces. It just wasn’t the right atmosphere to propose, so I decided to wait until we got home.

The difficulty was that I had put the entire box with ring into my pocket in anticipation of me barging into the restaurant and proposing immediately. It wouldn’t be easy to hide this during the dinner. I had a bulge the size of an orange in my right hand pocket, as I had Diana sit next to me on that side as well. Thankfully dinner didn’t last long as I finished the leftovers, but it was the longest 30 minutes of my life as I had to find ways of covering the bulge, deadly afraid of her putting her hand on my lap and asking what on earth I had in my pocket. I had to figure out a way to put it back into my work bag and ended up coming up with an excuse to go to the restroom right after we finished dinner. After awkwardly getting up, while putting my hands in my pockets in order to hide the bulge as I walked to the restroom, I eventually managed to take it out and put it in my bag. For once, something went right in the whole proposal plan, but it was definitely a close call.

My recommendation would be to wear baggy clothing so that it’s easier to hide the box without creating a huge and noticeable bulge somewhere on your body. This is definitely one of the marriage proposal tips that has to be on the list. For all I know, if she had found the bulge in my pants, she might have thought of something completely different going on.

#7 Don’t Take the First Reaction Too Literal and #8 Make Sure You Hold the Box the Right Way Up

When we finally made it home after dinner, the time was ripe, and I knew it was now or never. It was already late, and her parents must have been wondering at this stage why I hadn’t proposed yet. They must have been worried that I was having second thoughts, but they did not have to worry. I was still fully committed to go on with it despite the minor setbacks that I had experienced before.

As soon as I got down, before I even opened my mouth, and Diana noticed what I was doing, she yelled “Nooooo!” My heart sank immediately. I was pretty sure of the fact that I wanted to spend the rest of my life with her, and I was pretty confident that she felt the same, but all of that went out of the window as I saw her first reaction. What was I going to do?

Undeterred I decided to go for it as I certainly didn’t have anything to lose at this stage. As I grabbed the box out of my pocket, opened it up, and held her hand while I asked “Will you marry me?”, she said yes. I had done it! (It turned out that she simply yelled Nooo! as she was completely caught off guard with the proposal and that was her reaction) Phew… that was a close one!

As I reached into the box to grab the ring and put it on her finger I realized I was holding it upside down! Just one more thing that went wrong, but at least I was able laugh about it at this stage. I already knew that the answer was yes and nothing would change that at this stage. To top it all off, as I got the ring from the box it turned out it was about double the size it should have been. Diana had to literally squeeze her fingers together just for the ring to stay in place for the engagement picture we took right after, but it didn’t matter since I knew that I had done it.

So, my friends, even though I can laugh at it in hindsight, learn from my mistakes and take these marriage proposal tips into account when you plan one your girlfriend. That is, unless you want to go through the same when planning your proposal. You’ll certainly have a story to tell afterwards!